#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017852.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2017852
loop_
_publ_author_name
'Wilson, Colin R.'
'Munro, Orde Q.'
_publ_section_title
;
 Unconventional hydrogen bonding and π-stacking in two substituted
 pyridine carboxamides
;
_journal_coeditor_code           LN3145
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o513
_journal_page_last               o516
_journal_paper_doi               10.1107/S0108270110036218
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H9 N3 O3'
_chemical_formula_moiety         'C12 H9 N3 O3'
_chemical_formula_sum            'C12 H9 N3 O3'
_chemical_formula_weight         243.22
_chemical_name_systematic
;
N-(4-nitrophenyl)pyridine-2-carboxamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.162(4)
_cell_angle_beta                 97.147(3)
_cell_angle_gamma                112.760(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1490(3)
_cell_length_b                   7.3055(3)
_cell_length_c                   13.6613(5)
_cell_measurement_reflns_used    2788
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      31.9644
_cell_measurement_theta_min      3.0952
_cell_volume                     544.33(5)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 8.4190
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4092
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0778P)²+0.0252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                1722
_reflns_number_total             2148
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln3145.cif
_cod_data_source_block           II
_cod_original_cell_volume        544.33(4)
_cod_database_code               2017852
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H H3 1.536(3) 0.836(2) 0.7069(13) 0.060(5) Uiso d . 1 . .
H H2 1.410(3) 0.834(2) 0.5340(13) 0.054(4) Uiso d . 1 . .
H H100 1.117(3) 0.776(3) 0.4007(14) 0.062(5) Uiso d . 1 . .
H H12 1.171(4) 0.826(3) 0.1283(15) 0.083(6) Uiso d . 1 . .
H H11 0.824(4) 0.778(3) 0.0123(15) 0.072(5) Uiso d . 1 . .
H H10 0.454(3) 0.710(2) 0.0617(14) 0.063(5) Uiso d . 1 . .
H H9 0.444(3) 0.685(2) 0.2331(14) 0.062(5) Uiso d . 1 . .
H H6 0.722(3) 0.669(2) 0.5757(13) 0.055(4) Uiso d . 1 . .
H H5 0.839(3) 0.670(2) 0.7400(15) 0.070(5) Uiso d . 1 . .
C C12 1.0120(3) 0.7958(3) 0.14864(11) 0.0561(4) Uani d . 1 . .
C C11 0.8126(3) 0.7685(3) 0.07881(11) 0.0548(4) Uani d . 1 . .
C C10 0.5975(3) 0.7261(2) 0.10858(11) 0.0521(4) Uani d . 1 . .
C C9 0.5881(3) 0.7146(2) 0.20833(10) 0.0455(4) Uani d . 1 . .
C C8 0.7969(2) 0.74383(18) 0.27309(10) 0.0378(3) Uani d . 1 . .
C C7 0.7905(2) 0.73211(19) 0.38174(10) 0.0386(3) Uani d . 1 . .
C C1 1.0598(2) 0.75289(18) 0.53927(9) 0.0367(3) Uani d . 1 . .
C C6 0.8889(3) 0.7021(2) 0.59932(11) 0.0441(3) Uani d . 1 . .
C C5 0.9591(3) 0.7020(2) 0.69959(11) 0.0456(4) Uani d . 1 . .
C C4 1.1976(3) 0.75244(19) 0.73875(9) 0.0416(3) Uani d . 1 . .
C C3 1.3697(3) 0.8015(2) 0.68047(11) 0.0467(4) Uani d . 1 . .
C C2 1.3002(3) 0.8010(2) 0.58027(10) 0.0435(3) Uani d . 1 . .
N N2 1.0070(2) 0.78351(19) 0.24510(9) 0.0477(3) Uani d . 1 . .
N N1 1.0038(2) 0.75641(17) 0.43700(8) 0.0413(3) Uani d . 1 . .
N N3 1.2710(3) 0.75427(19) 0.84535(9) 0.0537(4) Uani d . 1 . .
O O1 0.60751(18) 0.70404(17) 0.41444(8) 0.0554(3) Uani d . 1 . .
O O2 1.1194(3) 0.7113(2) 0.89690(9) 0.0778(4) Uani d . 1 . .
O O3 1.4842(3) 0.7998(2) 0.87807(9) 0.0827(4) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C12 C11 . . 123.40(14) ?
N2 C12 H12 . . 116.4(12) ?
C11 C12 H12 . . 120.2(12) ?
C10 C11 C12 . . 118.93(14) ?
C10 C11 H11 . . 120.4(12) ?
C12 C11 H11 . . 120.7(12) ?
C11 C10 C9 . . 118.82(14) ?
C11 C10 H10 . . 121.1(11) ?
C9 C10 H10 . . 120.0(11) ?
C8 C9 C10 . . 118.30(14) ?
C8 C9 H9 . . 119.2(11) ?
C10 C9 H9 . . 122.5(11) ?
N2 C8 C9 . . 123.61(13) ?
N2 C8 C7 . . 117.25(12) ?
C9 C8 C7 . . 119.13(12) ?
O1 C7 N1 . . 124.87(12) ?
O1 C7 C8 . . 121.32(12) ?
N1 C7 C8 . . 113.81(12) ?
C6 C1 C2 . . 119.69(12) ?
C6 C1 N1 . . 123.42(12) ?
C2 C1 N1 . . 116.88(12) ?
C5 C6 C1 . . 119.81(14) ?
C5 C6 H6 . . 116.7(10) ?
C1 C6 H6 . . 123.5(10) ?
C4 C5 C6 . . 119.48(13) ?
C4 C5 H5 . . 122.1(12) ?
C6 C5 H5 . . 118.4(12) ?
C5 C4 C3 . . 121.74(13) ?
C5 C4 N3 . . 119.17(13) ?
C3 C4 N3 . . 119.09(13) ?
C4 C3 C2 . . 118.94(14) ?
C4 C3 H3 . . 122.4(10) ?
C2 C3 H3 . . 118.7(10) ?
C3 C2 C1 . . 120.33(13) ?
C3 C2 H2 . . 124.2(10) ?
C1 C2 H2 . . 115.5(10) ?
C8 N2 C12 . . 116.94(12) ?
C7 N1 C1 . . 128.59(12) ?
C7 N1 H100 . . 112.2(13) ?
C1 N1 H100 . . 119.2(13) ?
O2 N3 O3 . . 123.14(13) ?
O2 N3 C4 . . 119.16(14) ?
O3 N3 C4 . . 117.70(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C12 N2 . 1.3397(18) ?
C12 C11 . 1.380(2) ?
C12 H12 . 1.00(2) ?
C11 C10 . 1.368(2) ?
C11 H11 . 0.93(2) ?
C10 C9 . 1.387(2) ?
C10 H10 . 0.978(19) ?
C9 C8 . 1.384(2) ?
C9 H9 . 0.950(19) ?
C8 N2 . 1.3310(18) ?
C8 C7 . 1.5063(17) ?
C7 O1 . 1.2193(17) ?
C7 N1 . 1.3593(18) ?
C1 C6 . 1.3910(18) ?
C1 C2 . 1.394(2) ?
C1 N1 . 1.4039(16) ?
C6 C5 . 1.3841(19) ?
C6 H6 . 0.956(18) ?
C5 C4 . 1.375(2) ?
C5 H5 . 0.957(19) ?
C4 C3 . 1.378(2) ?
C4 N3 . 1.4662(17) ?
C3 C2 . 1.3812(19) ?
C3 H3 . 0.958(18) ?
C2 H2 . 0.973(17) ?
N1 H100 . 0.886(19) ?
N3 O2 . 1.2158(18) ?
N3 O3 . 1.222(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O1 1_655 0.973(18) 2.425(18) 3.277(2) 145.9(12)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C12 C11 C10 . . . . -0.2(3) ?
C12 C11 C10 C9 . . . . 0.8(2) ?
C11 C10 C9 C8 . . . . -0.9(2) ?
C10 C9 C8 N2 . . . . 0.4(2) ?
C10 C9 C8 C7 . . . . 179.97(12) ?
N2 C8 C7 O1 . . . . 177.22(12) ?
C9 C8 C7 O1 . . . . -2.4(2) ?
N2 C8 C7 N1 . . . . -2.50(17) ?
C9 C8 C7 N1 . . . . 177.90(12) ?
C2 C1 C6 C5 . . . . 0.8(2) ?
N1 C1 C6 C5 . . . . 179.92(12) ?
C1 C6 C5 C4 . . . . 0.0(2) ?
C6 C5 C4 C3 . . . . -0.6(2) ?
C6 C5 C4 N3 . . . . 179.33(12) ?
C5 C4 C3 C2 . . . . 0.4(2) ?
N3 C4 C3 C2 . . . . -179.57(12) ?
C4 C3 C2 C1 . . . . 0.5(2) ?
C6 C1 C2 C3 . . . . -1.0(2) ?
N1 C1 C2 C3 . . . . 179.78(12) ?
C9 C8 N2 C12 . . . . 0.2(2) ?
C7 C8 N2 C12 . . . . -179.34(12) ?
C11 C12 N2 C8 . . . . -0.3(3) ?
O1 C7 N1 C1 . . . . 0.7(2) ?
C8 C7 N1 C1 . . . . -179.59(11) ?
C6 C1 N1 C7 . . . . 6.6(2) ?
C2 C1 N1 C7 . . . . -174.23(12) ?
C5 C4 N3 O2 . . . . 0.0(2) ?
C3 C4 N3 O2 . . . . 179.90(13) ?
C5 C4 N3 O3 . . . . -179.94(13) ?
C3 C4 N3 O3 . . . . 0.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12173229
